Oh That ex girlfriend
by x.xOracles.Shadowx.x
Summary: The boys have a run in with Cassie in a little town in Ohio. Enough said.- *Destiel* Mentions of Sambriel.


**AN: Hi, guys!**

**I've recently started watching Supernatural, and I love Dean and Cas! They're so … Gah. They make my inner fangirl very happy. So, I was watching season one and 'Highway 666' just made me love Dean's character so much. He's so awkward with emotions, it's hilarious. **

**Also, I was reading another story about Dean and Cas having a baby and running into Cassie in, I think, it was a shopping mall (I can't think of the name of the author/ess or of the story, but it was hilarious, and I think a series of one shots. Go find it, this fandom has some very talented writers). That story came back to my mind while I was watching the episode. I messed around with ideas for a while and a few weeks later, this was born. **

**Now, just to get it out of the way, two things:**

**A) This is set after the apocalypse with Sam back and... re soulified, I guess you could say. Gabriel is still dead, but I couldn't not make a mention of him. He's such a bamf. (Also, I have Richard Speight Jr. on Twitter. So funny! Follow him. Follow him now. And follow me too, if you like: oraclesshadows. Shameless self promotion what?) So, Cas is an archangel, Sammy has his soul back, and Dean is still knee deep in denial over his warm and fuzzy feelings for our favorite archangel. Good times all around. **

**And B) I'm aware that Dean would be unable to be the godfather of Cassie's baby because he's legally dead. I get it, but this is fanfiction, so if I say he can be the godfather, then damn it, he will be. Because I am the authoress, and that is how I roll. **

**I think that's pretty much it. This is my first Supernatural fanfic, so I'm pretty excited. Since my name is not Kriptke, I clearly don't own them, so don't sue. Without further ado, enjoy!**

Sam figured it was the duty of the younger brother to mock their older brother for their previous girlfriends. It was like a rite of passage, and it was one that Sam Winchester had accepted never being able to indulge in. As much as he loved his brother, Dean didn't have enough women in his past who could be called ex girlfriends. There was Lisa, who Dean would swear deserved to be canonized into sainthood, and Cassie, whom Sam had affectionately called, 'The one who got away'. And that whole thing with Anna just didn't warrant mentioning. Of the two human women, Sam couldn't find any fault in them. Both were sincere, genuine women; both were smart, kind and caring; and both genuinely loved his brother. He still cringed at what Lisa and Ben had gone through while he was in Hell; Dean hadn't been the easiest guy to live with when Sam had been alive, so he couldn't imagine how difficult he'd be after watching his brother fall into Hell.

He and Dean were in Ohio for a by-the-book salt and burn of a vengeful spirit, Cas tagging along for a break from herding the ever rambunctious angelic host. Apparently, Uriel may have been the funniest angel in the garrison, but he was by no means the most ambitious. Cas had needed to, as Dean put it, lay an angelic beat down on quite a few of his more uppity siblings. If asked, Sam would deny ever chuckling at the news of Cas kicking Raphael's ass straight into the revamped Bible Boot Camp, run by Cas and the very vindictive Anna. The red head who'd had the honor of going face to face with a young Mary Winchester may've been raised back to Heaven, but she'd held on to a good old fashioned human love of petty revenge.

The brothers and Cas were driving through town, on the way back to the motel for some much needed rest, when Dean's cellphone began serenading them with the dulcet tones of Abba. Cas looked completely confused while Sam cackled in the backseat, ignoring the fuming glare Dean sent at him.

"You'll pay for that, Sammy.", Dean warned, then answered the phone with a brief, 'This is Dean.'

"Sam, what was that noise coming from Dean's phone?", Cas asked. Sam shook his head. The newest Archangel on the block knew lyrics to everything from Nine Inch Nails (An experience Sam NEVER wanted to bear witness to ever again. He still got a little queasy whenever 'Closer' came on the radio.) to AC/DC (He'd hummed 'Back in Black' for a week when Dean had been in the hospital. Sam would have killed him out of sheer annoyance if a) he wasn't so freaked out about his brother, and b) well... Archangel. Duh.), but he was completely unaware of anything that didn't involve harps, mullets or chains.

Sam was about to attempt to explain the broadway musical genre when Dead suddenly pulled a U-turn and rolled back up the street. "Uh, Dean? Hotel's back that way.", Sam pointed out.

"I know. Just got a call from an old friend of mine who lives in town. She saw the car and wanted to know if it was me.", Dean answered faux casually as he drove then pulled into the parking lot of a little cafe.

Sam pulled a classic 'Oh brother' bitch face as he got out of the car while Cas did the same. "When you say 'old friend', are we talking an actual friend or a -"

"Cassie!", Dean called, waving as a young woman walked over to meet them from the cafe door. Sam smiled, waving back, then his jaw dropped.

"A very pregnant Cassie.", Sam observed while Cas stood beside him in silence.

"This is the old friend Dean spoke of?", Cas asked, and Sam had the sudden horrible thought of Dean doing something really stupid to obliterate whatever it was that was building between he and Cas. He hoped the archangel would only make it rain hellfire or cause an earthquake in Arizona or something. When Cas was pissed, anything could happen, and even though Sam knew he wouldn't do anything to hurt Cassie or her baby, Dean was still fair game for smiting.

"Dean! Sam! God, I was hoping it was you!", Cassie greeted, giving the brothers hugs. She turned to Cas and smiled. "Who's your friend?"

Dean smiled, slinging an arm around Cas' shoulders. Sam rolled his eyes. "Cassie, this is Castiel. Cas, this is Cassie.", Sam filled in. "Forgive Dean, Cassie. As you know, he's socially retarded."

"I remember. Well, Castiel, it's nice to meet you.", Cassie answered, laughing and offering Cas a hand to shake. Cas smiled and accepted the hand while Dean's hand floated up and smacked Sam on the back of the head. Jerk.

"Likewise. And it seems congratulations are in order.", Cas responded.

"Thank you.", Cassie agreed, glowing. "We're very excited about her."

"'Her'? How far along are you?", Sam asked. "If you don't mind my asking."

"26 weeks, and Darren swears its a girl, but we're waiting until the birth to find out for sure."

"Darren? Never heard of him.", Dean commented.

"No, I met him on a story two years ago. We've been seeing each other ever since."

"That's great, Cassie. I'm happy for you. I'm sure you'll be wonderful parents." And Dean did look happy for her.

"Thank, Dean. That means a lot from you.", Cassie replied gratefully. "Say, Darren's going to be home around five, why don't you guys come by my place for dinner around six? If you don't have any other plans, that is." She gave Cas a covert look, and it was then Sam remembered that Cassie knew about their family business. Dean jumped, seeming to remember it as well.

"Cassie, Cas knows. He's... special." Cassie's eyebrow went up, and Sam could have smacked his brother.

"Not sure what that means coming from you, Dean.", Cassie told him.

"Cas is an archangel. The angel of Thursday, actually, but because of the whole apocalypse thing, he got promoted to archangel status.", Sam elaborated. Cassie's face slackened in shock.

"Wow. I take it back, you three have no choice but to come to my place for dinner. This is one story I have got to hear.", Cassie amended, grinning eagerly at them. Sam caught the quick flick of her eyes between Dean and Cas. Clearly, he wasn't the only one who could see through Dean's bullshit.

"We'd love to, thanks. Still at the old house?", Sam accepted, and quickly wrote down Cassie's new address, a house near her mother's where she and Darren lived. Dean swore to Cassie that the group would be on her doorstep at six o'clock, he and Sam receiving kisses on the cheek before the group parted ways.

The brothers and their archangel got in the Impala, and it was just as Cas was getting in the passenger seat that Sam noticed the tension of his shoulders and the frown on his face. Sam knew that expression well; there was a jealous archangel in the car. And Dean, as per usual, didn't notice a damned thing. It should have been expected; pit him against something supernatural and Dean could investigate, find it, kill it and be home in time for dinner with his hands tied behind his back, but when it came to emotions, it was like this blinder formed over his eyes, rendering him completely useless.

"So, what'd you think of Cassie?", he asked, driving up the road towards their motel. Cas sat in silence for a moment, and Sam sent a quick prayer to Gabriel that the car didn't blow up.

"Her soul is very clean, and she's good person. She loves you, and Sam.", Cas answered stiffly. Sam figured that Gabriel must have heard him because Dean gave the archangel a quick side glance in concern, but Cas was staring resolutely out the window. It was then that the younger Winchester knew it was going to be a very awkward three hours until dinner at Cassie's.

Sam, as usual, was right. When he was sure Dean and Sam wouldn't bleed to death in their crappy motel room, Cas popped out without another word. When Dean called him (beginning the conversation with a very eloquent, 'What the hell's your problem, dude?'), Cas only said that he would meet them at Cassie's at six, then hung up. This lead to Dean being in a very bitchy mood, calling Cas every ten minutes until the archangel turned his phone off (Sam bet the Metallica medley Dean had programmed as his ringtone finally did drive the saint crazy). This did not improve Dean's mood, and Sam quickly tuned out his brother's rant about telephones and archangels.

Three hours passed and ten minutes to six found the Winchester brothers driving to Cassie's house. As they turned into her driveway, they heard the rustle of wings and Dean looked at Cas through the rear view mirror.

"So you showed up after all.", Dean snipped.

"I said I would. I do not break my word.", Cas replied. He'd said it neutrally, but Sam wasn't imagining the venom in those words.

Dean put the car in park then shut it down and got out, his shoulders tense as he walked up to Cassie's front door, his boots thudding heavily against the wooden porch. Sam sighed as Cas got out, closing the back driver's side door with a little more force that strictly necessary, and followed Dean to meet Cassie and Darren, who were chatting on the porch. As the car stopped shaking, Sam considered praying to Gabriel to let them survive tonight without Cas smiting Dean, but reconsidered. Though he may've come over to their side of the apocalypse, Sam didn't think that put him above finding a lover's brawl between an archangel and a closet case hunter seven different types of hilarious. Sam, grudgingly accepting of the inevitable, got out of the car and walked towards his fate with a smile.

Dinner, much to Sam's shock, went well. Darren, a thirty one year old photographer working out of Ohio, proved to be an engaging, funny guy who worshiped the ground Cassie walked on. The group sat together around the dinner table, trading stories. They chatted and eventually, Cassie revealed that Darren knew about Sam and Dean's family business. This normally would have resulted in equal parts outrage and tears, and Cassie, seeing the clouds looming over Dean's face as silence pressed around them, hurried to explain. Dean let out a huff of air and Cassie took his hand. "Cassie, how many people have you told?"

"Just Darren. I promise, Dean, I've kept your secret, but I needed to tell him."

"Why? Cassie, do you have any idea how much trouble Sam and I could get in to? If anyone finds out, we'll have the cops on our tails from now to the next judgment day!", Dean told her, frustration stamped on his face.

"Dean, just calm down-", Sam tried.

"I needed him to understand why I wanted to ask one of my exes to be our baby's godfather. It's kind of a weird request to make without some background information, don't you think?", Cassie asked.

"Wait, what?" Dean looked thunderstruck, and Sam knew that his mouth was hanging open. "You want me to be- Cassie, I can't-"

"Dean, just hear me out. After everything you and Sam did to help my family when... my dad died, I never forgot. When I found out I was pregnant, I knew what hung out in the shadows and I knew what it could do. I wanted my baby to be safe if, God forbid, something ever happened to Darren and I. I can't think of anyone I would trust more to protect our child than you, Dean.", Cassie explained. "I needed to tell Darren so he didn't think I was using our baby to bring you back into my life."

"Cassie, I'm telling you right now, you, Darren and the baby will always be safe, you have my word. Nothing will ever happen to you and your family as long as me and Sammy are breathing.", Dean assured her.

"I know, Dean, and I love you guys for it. But, like I said, if something ever did happen, I want to know for a fact that someone will be there to keep him or her safe. After what happened to my dad, I was scared to death, but you and Sam figured out what was happening and stopped it. I felt safe, knowing you two were going to fix whatever was happening. I want our child to have that security. If we're not there, I want to know that you and Sam will keep them safe and find out what happened."

"I'd do that even if I wasn't the godfather, Cassie. But you know I'm no good with kids."

"You think we are? We're going into this parenting thing blind, Dean.", Cassie laughed. "It's a learning experience, and if you guys can hunt ghosts, kill demons and stop an apocalypse, I think you can handle a kid."

"It's debatable.", Dean muttered, then ran a hand through his hair. "I mean – Jeez. Cassie, I don't know what to say here."

"How about yes? It would mean the world to me.", Cassie offered.

Dean exhaled, then looked at Cas over the dinner table. Sam couldn't see anything visible change on his face, but Dean clearly could because a smile lit up his face.

"Cassie, Darren, I think you're both nuts for trusting me to raise a kid, but I'm honored. If you want me as a godfather, you've got me.", Dean told them, bringing a smile to both Cassie and Darren's faces. "However, I'm telling you right now, you two better not go getting into trouble until the kid is old enough to tie his own shoe laces. And, the kid will be able to swear in three different languages by the time they're ten. Two of those languages not being human."

Darren laughed and Cassie shook her head. "Thank you. If half of what Cassie says about you two is true, I'll be able to sleep at night.", Darren answered, shaking hands with Dean. As the dinner plates cleared from the table, the smell of fresh baked apple pie filled the house and Dean looked like he'd just landed in heaven. Dean, Sam, Cassie and Cas chatted in the living room, with Cassie asking Cas questions about the angelic hierarchy, as well as the actual duties of the host, while Darren saw to coffee and dessert (tea for Cassie and Cas, which Dean found more creepy than funny).

Hours flew by and before anyone knew it, it was nine at night. Cassie stood from the couch, taking the cups and saucers from the table and waving off Darren's offers of help. "I'll be fine. You just stay and keep our guests company. Hey Dean, grab that tray for me, would you?", Cassie asked. Dean rolled his eyes and Darren shrugged in helplessness as Sam laughed when his brother stood and picked up the tray.

The two vanished into the kitchen, and Cas' eyes followed them until they were out of sight. Sam tried not to worry about his brother being smote and jumped into a conversation with Darren. (Most guys had to worry about their brothers getting STDs and pregnancy scares. He had to worry about his brother being turned into a pillar of salt for cheating on an archangel.)

When Dean and Cassie returned, Dean's face was bright red. Sam soon got the shock of his life when his closet case, 'No-Chick-Flick-Moments', 'Grow-a-pair-you-pansy' brother sat next to Cas on the sofa, then took his hand. Cassie was beaming as she sat down, and Sam thought that Cassie was probably the only woman on Earth would could not only accept but be happy that her demon hunting ex was in love with an angel in a human suit. He was burning with curiosity about what she'd said to Dean in the kitchen, but had a pretty solid idea.

It was quarter to eleven when Cassie began yawning and Dean and Sam began making their excuses to leave. Cassie gave the three hugs and made them promise to keep in touch with she and Darren. Dean swore on the Impala that the second the call came through that the baby was on the way, they'd be burning down the highway as fast as his baby could go.

As the group walked out to where the car was parked, Cassie asked Cas for a quick minute alone. Dean stood by the car while Sam and Darren chatted about some article both had happened to read and watched Cassie and Cas talk on the front porch with nervous eyes. "Uh, hey, Darren.", Dean interrupted quietly, his eyes never leaving his ex girlfriend and his current... whatever he and Cas were.

"Yeah, Dean?", Darren asked.

"Be honest with me. What is she saying to him?" Dean looked like he was a short cry from sweating where he stood, and Sam could only snicker.

"I haven't got a clue, Dean. You know yourself how Cassie's mind works. Just expect the unexpected.", Darren advised, giving Dean a pat on the shoulder in sympathy as the older hunter visibly deflated.

"Yeah, that's what I was afraid of.", Dean replied, going slightly pale.

"Dean, calm down. Cas has seen your soul and every immoral thing you've ever done. After all of that, he still loves you, so just quit worrying.", Sam tried to reassure him, and his words caused Dean to choke on oxygen.

"Sammy! Ixnay on the ove-lay ord-way.", Dean hissed, checking over his shoulder quickly to make sure neither Cas nor Cassie had heard him.

Sam merely shook his head and kept his silence. Dean would never change entirely, but Cas seemed to bring out the softer sides of him that Sam hadn't seen since he was a kid. Sam decided to let go of the reigns and let his brother stumble blindly through his mini gay freak out. Dean would grow a pair eventually, and as always, Sam would be waiting for him to man up and listen paitently as he admitted the truth. If he was armed with a hearty 'I told you so', well, who could blame him?

When Cassie and Cas rejoined them, Cas sent Dean a smile so warm that Sam could practically see his brother's insides melting. And he called Sam the girl.

"Well, Cassie, Darren, once again-", Sam began, trying desperately to avoid the staring contest going on behind him. Honestly. When they finally got past the eye sex to the actual sex portion of the relationship, Sam would thank his lucky stars, if he had any left. And book a separate room on the other end of the motel, but that was neither here nor there.

"Sam, you don't need to thank us anymore than you already have.", Cassie told him, smiling at the silent conversation going on between Dean and Cas. "It was nothing. I'm glad you both could make it and meet Darren. It was great seeing you guys again, so don't be strangers okay?"

"We won't. Next time we're in the area, you'll be the first person we call, promise.", Sam answered, smiling at she and Darren. He turned to where his brother stood shoulder to shoulder with his angel, and noticed that neither seemed too keen on coming back to the real world anytime in the near future. 'Well, no one said that being an awesome little brother came easy.', Sam internally sighed. "Dean, Cas, come on. Gotta get rolling if we're going to leave early tomorrow morning."

"Yeah, we heard you, Sammy.", Dean answered, pulling his eyes away from Cas. He made a show of hugging his ex girlfriend before shaking hands with Darren, a genuine smile on his face. "We'll be seeing you two soon enough, alright? Darren, it was great meeting you. Take care of Cassie and my godkid, and if either of you need us-"

"You're a phone call away.", Darren finished, grinning.

"Don't forget it. And Darren? You're a good guy. I'm glad Cassie found someone who can make her happy.", Dean confessed, sitting in the driver's seat of the Impala.

"Right back at you, Dean.", Darren returned, smiling as Cas sat in the passenger seat without question while Sam stretched out on the backseat.

Dean blushed, then roughly cleared his throat while Cassie smiled wickedly beside Darren. "Yeah, thanks. Well, see you guys in a couple weeks, alright?"

"We better. Call me when you're on your way, I'll make sure we have a couple rooms set up for you.", Cassie promised.

"Will do. Have a great night, guys, and say hi to your mom for us, Cassie.", Dean replied then let the Impala roar to life. Cas and Sam waved in farewell as Dean drove out of Cassie's driveway.

"That was a very pleasant evening.", Cas commented as Black Sabbath bled from Dean's speakers. "Cassie and Darren will be very happy together."

"Yeah, I hope so. They seemed pretty solid.", Dean agreed, steering the Impala through the night. He flicked his eyes to the rearview mirror. "Can you believe it, Sammy? Cassie and Darren want me to be their kid's godfather."

"It's an honor alright. I'm proud of how you handled tonight, by the way. Very mature. Sure you're feeling okay?", Sam asked from where he lay on the backseat.

"What are you talking about?"

"Dean, you just had dinner with the girl you confessed to being in love with and the father of her unborn child. Not many guys can do that."

"Sam, Cassie and I were a long time ago. I'm just glad she's safe and happy.", Dean argued.

"Dean, you almost cried when we drove away from her the last time. You let me drive your car without question!" Sam was trying to give Dean an opening for him to reassure Cas, but typical Dean, he wasn't making it easy.

Dean exhaled harshly, noticing that Cas was listening intently. He scrunched up his face, then sighed again, seeming to realize that he was caught.

"Okay. Yes, I lov- cared deeply about Cassie, I don't deny that. She was the first woman I ever felt close enough to to tell our family's little secret. She'll always have a place in my heart, but I don't love her romantically anymore. I'd take a bullet for her, but that's it. I've moved on, she's moved on, and everybody is finally happy."

Sam had to give him credit ,that was one hell of an answer. Even Cas looked impressed.

"That reminds me. What were you two so buddy-buddy about, Cas?", Dean asked, and Sam decided not to analyze that thought process. He thought it pretty much spoke for itself.

"Cassie wished to speak to me. She wanted to know if there was anything she could do to ward her home and family against any negative forces near by. I assured her that there was not, but she was persistent. I advised her on some protective talismans she could look in to, as well as some precautions to take. And she asked about us."

Dean turned purple, and Sam cursed both his luck and his mp3, which he'd left back in the motel. This was one conversation that he was pretty sure he didn't want to hear.

"'Us'?", was all Dean asked.

"She asked me if we were happy. I told her that we were, and she asked me to keep you safe and happy in a way that she could not."

"And, uh, what did you say?"

"I said that I would protect you from anything on Earth, or in Heaven or Hell. She began crying at that and said something about hormones. Once she'd calmed down, she said she was relieved we had found each other, 'even if it had taken a trip to hell and an apocalypse'. She wished us all the best, then we spoke of biblical baby names she and Darren could consider for the baby. I suggested Rachel for a girl, and Gabriel for a boy. She seemed fond of them.", Cas relayed, catching Sam's eye in the rearview mirror as he said Gabriel. Sam turned a slight red then found a spot on the ceiling to be utterly fascinating.

"Huh. Good ol' Cassie. She said the same thing to me in the kitchen.", Dean said smiling, driving on. Sam could see the fluorescent lights of the motel in the distance, and he stifled a yawn.

"Yes, she mentioned..."

Cas's voice mixing with Dean's and the music from the stereo formed a lullaby that soon made Sam's eyes heavy. He threw his coat over him and got comfortable, letting his brother and Cas' voices lull him into sleep, surrounded by family. Maybe he would sleep in the Impala tonight, it sounded like Dean was actually acknowledging his feelings and who was Sam to get in the way of that?

This was family, right here. Him, his brother, and their resident angel, driving through the dark. It wasn't nuclear or normal, but Sam would take it and run to the ends of the Earth if it meant it was safe. For the first time in a long while, Sam Winchester fell asleep with a smile on his face.

**That's it for now, guys. I have no internet out here so I need to use the internet when I can find it. Let me know what you think! **

**Much love and thanks for reading!  
>Oracle. (L) <strong>


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